Water → HCID 62385806, compound

HRID 1615759Notes

Reaction equation

HRID 1615759 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:9][CH:10]([CH:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1)[C:11]([O:13][CH2:14][CH3:15])=[O:12].C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[CH2:1]([NH:9][CH:10]([CH:16]1[CH2:17][CH2:18][O:19][CH2:20][CH2:21]1)[C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 15946566HCID 15946566, compound

Product 1

HCID 62385806HCID 62385806, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.53 ml (4.5 mmol) benzylbromide, 0.85 g (4.5 mmol) ethyl (rac)-amino-(tetrahydropyran-4-yl)-acetate and 1.9 g (13.7 mmol) potassium carbonate in 10 mL DMF were stirred for 2 h at 100° C. After cooling the mixture was mixed with water and extracted three times with ethyl acetate. The combined organic phases were extracted with saturated, aqueous saline solution, three times with 0.5 M hydrochloric acid and once more with saturated saline solution. The combined aqueous phases were adjusted to pH 9 with conc. aqueous ammonia solution and extracted three times with dichloromethane. The combined organic phases were washed with saturated saline solution, dried and concentrated by rotary evaporation.

Workup

  1. temperatureAfter cooling the mixture
  2. extractionextracted three times with ethyl acetate
  3. extractionThe combined organic phases were extracted with saturated, aqueous saline solution, three times with 0.5 M hydrochloric acid
  4. extractionextracted three times with dichloromethane
  5. washThe combined organic phases were washed with saturated saline solution
  6. customdried
  7. concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record
ord-77fa5a093db840ecab494b4a0dbc9b95
Source dataset
uspto-grants-2014_07
Patent number
US08765763B2

Reaction notes

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